Nitrogen → 3-chloro-4-(chloromethyl)pyridine hydrochloride

HRID 1709949Notes

Reaction equation

HRID 1709949 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.S(Cl)([Cl:12])=O.N#N.[O-]S([O-])(=O)=O.[Ca+2]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][Cl:12]

Participants

5

Reactant 4

HCID 947NitrogenHCID 24386Thionyl ChlorideHCID 24497Calcium SulfateHCID 12742466(3-Chloropyridin-4-yl)methanol

Product 1

HCID 230350493-chloro-4-(chloromethyl)pyridine hydrochloride

Procedure

Solid 3-chloro-4-hydoxymethylpyridine (33.8 g, 0.235 mol) was added cautiously over 8 min to stirred thionyl chloride (72 ml, 0.706 mol) cooled in an ice bath and under a stream of N2. After addition the yellow solution was heated in an oil bath at 50° and protected under a tube of Drierite. After 30 min the solution was removed from the oil bath, allowed to cool to ambient temperature, and poured into a flask of stirred anhydrous ether (1,000 ml).

Workup

  1. additionAfter addition the yellow solution
  2. temperaturewas heated in an oil bath at 50°
  3. customAfter 30 min the solution was removed from the oil bath
  4. additionpoured into a flask of stirred anhydrous ether (1,000 ml)

Sources & evidence

ORD record
ord-fa0bb27bf4f64b5ea4418d283ac3a14f
Source dataset
uspto-grants-1990_08
Patent number
US04952397

Reaction notes

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